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Erika's Adventure Part One - A Whole New World free porn video
All of my stories are complete fiction, all the characters and situations
are also fiction. You should be at least 18 yrs of age to be reading
this. This is the adventure of a young twenty something tgirl, who is on
a journey of self discovery, and her adventures and mishaps along the way.
Some stories involve sexual content and the main story is about sex, while
other stories involve Erika's day to day routines. I hope you enjoy it.
Erika's Adventure - Whole New World. Part one
This is the first part of what will hopefully be several different
fictional stories of a young man's adventures as a transvestite or Tgirl.
I hope you enjoy :)
I've been a transvestite since I was a little kid. I mean at the time I
had no idea what I was doing, but I was fascinated by girl's clothes and
makeup. I was no sissy by any means, I liked playing sports and I was
actually quite tough when I had to fight. The earliest time I could
remember having the urge to dress was when I was ten; my parents were
going out of town with my older sister, Sabrina, who was 14 at the time.
I was staying behind because I was going to tennis camp. My older cousin
Jennifer was babysitting me for a few days. Jennifer was 18 and she was
beautiful, she always dressed very sexy and was always done up with makeup
and nails, and she always had high heels on, and to this date I think
that's where I get my love for high heels. Anyways Jennifer was very nice
and we had a good time together. Through our time together I began to
wonder what it would feel like to wear her clothes and her high heels. On
the second day with Jennifer I decided that I would sneak away from tennis
camp after Jennifer dropped me off and I would head home to try on her
clothes and maybe my sisters. I was able to sneak out without being
caught. No one was home so I snuck into my sister's room, that's where
Jennifer was staying. I was too nervous to try on Jennifer's clothes so I
found a cute dress from my sister's closet, I put on her bra and her
panties, and I remember stuffing some socks in the bra. I was going
through her shoes trying to find a cute pair to wear, but I couldn't find
anything I really liked. I did notice a pair of Jennifer's black high
heels, I tried them on and quickly found that I could not walk in them
very well, but they did look great on me. Looking in the mirror with my
summer dress and high heels I loved the way I looked. I really liked the
way the dress would sway when I walk and how the high heels would click on
the hardwood floors. I decided I was being brave so I put on some girlie
music and started to dance. I grabbed some pink lipstick from my sister's
drawer and carefully applied it to my lips. I was feeling so girlie, it
was so much fun, and I was getting a bit better adjusting to the heels. I
was a lot of fun dancing as a girl and I was lip-syncing to the Britney
Spears song. With the music still playing I decided to grab a purse from
my sister's closet, I grabbed a cute white purse and when I came out of
the closet I was shocked to see my cousin Jennifer standing there with a
shocked look on her face. I can still remember the look on her face, she
was surprised but she was also holding back the laugher. For me it was
the worst thing in the world, I was caught in my sister's room in her
dress, with lipstick on, and I was dancing in Jennifer's high heels. All
I could say was, "oh my god Jennifer, I'm so sorry, I shouldn't be doing
this, I'm so sorry. Jennifer just looked at me and asked me what I was
doing dressed up like this. I told her I don't really know why I was
doing this, that I just felt like trying on the clothes. I began to cry
and Jennifer came over and gave me a hug. She sat me down on the bed, and
told me that it was okay and that I didn't need to cry. We talked for a
bit, she wanted to know how long I have been dressing up like a girl, I
told her this is the first time and that I would never do it again. She
told me that I actually made a pretty cute girl, she said that I would
look really good if I had long hair like a girl, and she told me she was
jealous that I was wearing her heels, she said she wasn't able to wear
heels until she was 15. We both laughed and it made me feel a bit better.
I asked her if she was mad at me and if she was going to tell my parents
and my sister Sabrina. She hugged me and told me that she wasn't mad and
that she would keep this secret between them, but she said I needed to be
a bit more careful so that I wouldn't get caught again. My parents were
coming back that night so Jennifer told me to talk off my sister's clothes
and helped me wipe the lipstick off. We never really talked about the
incident again, Jennifer was off to college later that month, and the
family put on a little going away party. Jennifer was especially nice to
me ever since my first dress up incident. After the party Jennifer pulled
me to the side and handed me a box, she said it was for me. I opened it
and it was full of her old clothes, there were two dresses, a few skirts,
some tops, a bra and some panties, one pair had the word juicy on it.
There was a purse and inside the purse was some makeup and some nail
polish. There was also a pair of high heels, the same ones I wore
earlier. I was shocked by all of this and I didn't know what to say but I
was very excited. She told me that I could keep everything that she
outgrew them and since she didn't have a little sister that I could have
them. She joked that I was quite lucky, that normally this would be going
to my older sister. I told her thanks and she said that it was okay if I
liked to dress up like a girl, but that it was very important that I was
careful when I did dress up. She gave me a wink and said goodbye, I
quickly took the box to my room and hide it in the closet.
From the ages 10-12 I would dress up any chance I could. I didn't have
much time to myself but it was a lot of fun going through Jennifer's stuff
and playing dress up. I was very care not to get caught and I did wear
some of Sabrina's stuff from time to time but I was always careful to
return everything. By the time I reached 13 I was so busy with school,
and I was a very good tennis player and I was a very good swimmer. I
guess I just grew out of dressing up and between the ages, 13 to 19 I
didn't dress up once, in fact I had thrown out all of the clothes Jennifer
gave me, including the high heels, which didn't fit me anymore. I also
had a girlfriend and I was pretty much living the life of a normal 19 year
old. I just entered college and I was about to return for a second
semester when I had a serious knee injury while skiing. I needed surgery
and I was never able to return to competitive tennis again. It took me
quite a while to rehab my knee and I had a very difficult time. I was
very depressed, my girlfriend left me, and I started to put on weight. I
had thought of dropping out of school, but I knew how important it was to
my parents and they were paying for my schooling so I kept up with it, but
my marks did suffer. I still hung out with my friends but I was spending
more time at home by myself. At home I spent a lot of time online, I
played some video games but I was also looking at a lot of porn. I am not
sure why but I began to search a lot of transgender porn. I was so turned
on by these hot trannies and shemales. I would masturbate quite often,
but I would always imagine myself as one of the trannies. I never really
thought of having sex with a man, I know I used to love dressing up like a
girl, but I never really found men attractive, but looking at all this
porn I truly wished I was one of those tgirls having sex with a man. It
was at this time that I had the urge to dress up again. My sister was in
her last year of teacher's college so she wasn't at home but she did still
have some of her old clothes around. I would dress up when I could but
her clothes were a bit too small for me. I wasn't a very big man, I was
only 5'7 and although I put on some weight I was only 190 lbs, too fat for
a girl, but not bad for a guy :) I managed to find some things of my
sister's to wear and I gathered enough courage to buy a few things of my
own. When I was alone at home I would dress up and I would chat online.
I enjoyed being girlie and I took on the name Erika. I loved chatting
with other tgirls, they would give me some tips and we would talk about
why we liked to dress up as girls. I would get hit on all the time by
horny men, but I wasn't really interested, although I did love getting the
attention. One weekend, my parents were heading down to see my sister at
college and I was able to spend the entire weekend as Erika. On the
Friday night, a guy named Gregory started chatting me up. He seemed like
a nice guy, although you never know when you are talking online. We
talked for a few hours; we talked about everything from my dressing to
tennis, and movies. Later on in the evening he told me some stories about
past tgirls that he used to date. I had to admit it was turning me on to
hear about him having sex with a tgirl. He asked me about my experiences
with men, and I told him I have never dated a man before. He asked me if
I was going to be online the next night and that he would love to chat
with me again. I told him I should be online tomorrow, we said goodnight
and I logged off the computer. Before going to sleep I started to
masturbate and I was fantasying about having sex with Gregory. I imagined
I was sucking his cock and that he was fucking me in the ass, I was so
turned on that I came right away. I went to sleep with a big smile on my
face :)
The next morning I woke up and grabbed some breakfast, I turned on the
computer and noticed that I had an email from Gregory. He said he had a
good time chatting last night and that he was looking forward to chatting
again. He also attached some photos, he was an okay looking guy maybe 25,
he was a bit overweight but not too bad, he also sent me a photo of his
erect cock. I wasn't really shocked to see the cock pic as other men have
sent me pics, but I was chatting with this guy and I was surprised to see
he sent me a pic of his hard cock. I wasn't really offended or anything
in fact I couldn't stop looking at it. I was never really attracted to
men, and a man's cock, but when I was dressed up I did wonder what it
would be like to be on a date with a man, where he was treating me like a
woman. I didn't really care if this made me gay; as I think gay is just a
word. Anyways I went about my day, I went for a short bike ride in the
morning, but I kept thinking about Gregory. That afternoon I went to mall
which I would sometimes do, and I just sat on one of the benches people
watching. I loved to watch the girls at the mall; I was intrigued but
what they were wearing, their heels, and their hair and makeup. I also
watched their mannerisms, they way the swayed, swung their arms when they
walk, the way they would play and flip their hair. On this day I was also
watching the girls with their boyfriends, how they held hands, and how
they laughed together. I had to admit that I thought it would be pretty
fun to be out at the mall with my boyfriend. As I left the mall, I passed
by the drug store and decided I would buy a new lipstick that I could wear
later that night. I walked through the makeup aisle loving the smell of
makeup and perfume, I stopped at the lipstick sections and I started
looking for something I would like. There were hundreds of lipsticks, so
hard for a girl to decide. I was incredibly nervous and looked around to
make sure no one was watching me, just as a reached for a covergirl
lipstick one of the salesgirls came up to me and asked me if I needed any
help, she even called me "hun." I was so freaked out that I just looked
at her and started to walk away, as I looked back she has a little smile
on her face, she must have known I was a little sissy, looking to by some
makeup. Oh well I chickened out and I didn't feel very good about myself
so I went home.
Later that evening I started to think about Gregory again and I opened his
email and was checking out his photos. I was so turned on by his cock
that I decided to get all dolled up again. So I got undressed and put on
my black panties and tucked myself all away, next was my bra, then my nude
stockings. I wasn't very hairy and the stockings covered up any hair I
did have. I was going with a black mini skirt with a red blouse. I went
with my black three inch heels, I always love putting my heels on as I get
all dolled up, it just made me feel extra feminine to walk about in my
heels. I had a cheap blond wig and I did my full makeup. I decided
tonight to add a little perfume and to paint my nails. Once I was done I
looked pretty good and I immediately started acting girlie. I turned on
my computer again and entered the chat room. There were some people
online that I would occasionally chat with but truth be told I was really
hoping that Gregory was only. I chatted for a bit and then decided to
take some photos of me all dolled up. It was starting to get late and I
was actually a bit upset that Gregory told me he was going to be online
but that he wasn't. Is this what teenage girls go through when guys do
not call them? I was just about to shut the computer off and head to play
some video games when I got an IM from Gregory. I was so excited that he
contacted me that I immediately wrote him back. We chatted for a bit and
I told him about my makeup buying experience and he told me that I didn't
have anything to worry about. He then asked me what I was wearing, so I
sent him some photos. He said he really liked them, and then he asked me
if I liked the photos that he sent me the evening before. I told him that
I did like the photos and that I thought he was a handsome man. He then
asked me if I liked the photo of his cock. I paused a bit but then I told
him that I did enjoy it, that I was surprised that he sent it to me, but I
did like it. He told me he took that photo while thinking of me. He told
me that I was very cute, and that I had to expect that I would turn men on
with the way I look. He then asked me about my experiences with men, and
I told him that I had not had any experiences. He asked me if I was
attracted to men, and I told him that I wasn't sure. He then asked me if
I found him attracted and if I was turned on when I looked at the photo of
his cock. I was trying to be honest with him and I told him that I did
find him attractive and that yes I did look at his cock photo quite often.
He told me that there was nothing wrong with being attracted to men, that
many girls like me really enjoy dating me and having sex with men. We
continued our chat for a while, and then he asked me what my plans for the
night were. It was already 11pm so I didn't have any plans. He asked me
if he could come over and hang out. I waited a bit but I told him that I
don't think that would be a good idea. He said he understood but said
that he would really like to meet me. He then asked me if I would like to
go over to his place, he lived in a condo downtown. I told him it was
late and that I should probably just go to bed. He said he understood,
and truth be told I was very turned on by our chat and I was very curious
what it would be like to be with a man. We chatted for a bit longer and I
was still turned on, when he asked me one more time if I would like to
come over to chat and maybe have some wine. I hesitated for a bit but
then I just said, "sure." I can't believe I just said that but I was still
pissed off that I chickened out earlier with the lipstick, that if I
wanted to look and act like a girl, that I should try dating a man. I
didn't want him to pick me up at my place so we decided to meet at a local
mall. I would take my car and meet him there and he would drive me to his
place. I checked over my outfit, re-did my makeup. I grabbed my purse
and put my keys, some more makeup and some money into my purse. I headed
out the door and I was unbelievably nervous. Once I got the mall parking
lot, another car pulled up beside me. Gregory got out and I got out of
the car to meet him. Gregory was quite handsome, he was about 30 years
old, he was about 6 feet tall with an average build. He had a goatee. He
drove a very nice BMW. We exchanged hellos, he gave me a hug then opened
his car door for me. This was the first time a man has ever seen me
dressed up like Erika. It felt nice that he opened the car door for me.
Once inside his car he told me that I smelt really nice and that I had
very sexy legs.
Once we got to his condo, he held the elevator door for me. He could tell
that I was very nervous and told me to just relax, we were just two people
hanging out on a Saturday night. Inside his apartment he showed me around
and he had a very nice place. He handed me a glass of wine, I don't
normally drink wine but I thought I would give it a try and it may calm my
nerves. We chatted for a bit in his kitchen, he told me how cute I was
and how I would make a beautiful bride one day. We both had a laugh and I
was getting a bit more comfortable. After about five minutes of small
talk, he grabbed my hand and took me to the living room. I never held a
man's hand before but it felt nice. He said we should have a seat on the
couch, that it would be more comfortable. He grabbed the bottle of wine
and gave me a bit more. We sat on the couch and we chatted some more. He
then put his hand on my knee and once again complemented me on my sexy
legs, I told him it was from all the tennis I used to play. We smiled at
each other, but he kept his hand on my leg. Just then there was a knock
on Gregory's door. He got up to answer it. He was chatting with someone,
sounded like a neighbour. I decided to take this time to touch up my
makeup, so I took my lipstick out of my purse and my compact and I
reapplied my lipstick. As I was putting on some more lipstick, Gregory
came back into the room. He apologised for the interruption. He noticed
I was fixing my makeup and he made a joke about us girls and always
worrying about our makeup. He sat back down and complimented me on how
good my lips looked. I smiled and thanked him and put my compact and
lipstick back into my purse. As I sat back Gregory leaned forward and
kissed me on my lips. I was a bit shocked, but not totally, after all I
was dressed up like a girl, sitting on a man's couch. I kissed him back.
It felt a bit weird as his goatee scratched my face, but it felt nice to
have a man make the first move. We continued kissing, and he slid his
tongue into my mouth, and I accepted his tongue as we made out on the
couch. As the kissing continued, Gregory put his hand back on my thigh
and was rubbing my leg. I could tell he was totally turned on. He then
grabbed my hand and put it on his crotch. I could feel his raging hard on
through his pants. He was making me rub his cock through his pants as we
continued to kiss. Soon enough he let go of my hand and I continued to
rub his cock. I couldn't believe I was here, dressed up like a girl,
making out with a guy, while I rubbed his cock. His cock felt so big, so
hard. He now moved his hand up my leg so that he was at my panties. He
slowed down a bit, and asked me if I was doing okay, I smiled and said
yes, and he began to rub my crotch over my panties. I was so turned on
that I came right there. I was so embarrassed, but it felt so good, I've
never came so quickly before this was wild. We continued making out and
he was still feeling me up, I still had my had on his crotch feeling his
hard cock under his pants. He was moaning with pleasure, and he told me
to take his cock out. I was about to when I quickly realized that I was
about to suck another man's cock soon enough at this rate. I broke off my
kiss and told Gregory I had to use the ladies room.
I grabbed my purse and once inside the washroom, I looked in the mirror
and saw this girl looking back, knowing I had just made out with a man, my
lipstick was a mess, but the biggest thing was that I really enjoyed it.
Looking at the mirror I knew that if I went back out there, Gregory was
expecting me to suck his cock, I knew that that is the way it works. He
was a man and he had needs, my ex girlfriend gave me a blow job once, but
said she didn't like it so I wasn't exactly sure what to do. I have seen
my share of porn but this was for real. I knew if I went back out there,
there was no turning back. I could always just leave and go home, but I
took a deep breath, fixed my makeup and my hair, checked myself in the
mirror one last time and I tucked my purse under my arm and I went out to
see Gregory. The clicking of my heels only turned me on more. Once I
returned to the living room, he asked me if everything was okay, I told
him yes and I gave him a smile. He grabbed my hand again and lead me back
to the couch, we sat and he told me what a great kisser I was, he told me
that I had the lips of a woman, very soft. They he said, "now where were
we?" I smiled and played a bit coy, saying I wasn't sure. Then he said
that I was just about to feel another man's cock in my hand. With that he
kissed me again and held me tight, he grabbed my hand and put it on his
crotch, I didn't fight him, I once again began rubbing his still engorged
cock. He told me that felt really good. With that I broke off my kiss
and began to unzip his pants, I still remember how cute my painted nails
looked lowering his zipper. I reaching in and pulled out his cock. I
couldn't believe how warm it was, and he was pretty big, about seven and a
half inches. As I grabbed it he let out a long moan. He then told me to
wait so that he could take off his pants, which he did along with his
underwear and socks (why do some guys leave their socks on :) He sat back
down on the couch and I once again wrapped my hand around his unit. Like
I said he was seven and a half inches but he was pretty thick as well. I
couldn't believe I was sitting here dressed up as a girl with another much
older man's cock in my hand, but the most incredible thing was that I
couldn't believe how smooth his cock was. I felt my own cock a million
times and never realized how smooth it was. Anyways his cock felt really
good in my hands, I touched every inch of it, I was studying it. It was
quite obvious now that I had no problem being with a man and in fact I
quite enjoyed it. We began to kiss again as I continued to explore his
manhood. I was playing with his mushroom tips for a while which he
enjoyed then I began to rub his heavy hairy balls. We kissed for about
another minute, when Gregory broke off the kiss and told me my hands felt
so good on his cock. I smiled and said thank you, when he told me, "Why
don't you be a good girl now and put those beautiful pink lips around his
cock." He smiled at me, "I know that's what you really want sweetie, from
the first time I saw those glossy lips I knew it was only a matter of time
before they were wrapped around my lips, so go for it baby." I was a bit
shocked by his words, but truth be told, I was dressed up like a girl over
at his apartment and I was pretty much giving me a hand job, so I
shouldn't be surprised that he was so forward with me. So I gave him a
little smile and I knelt down before him with him still sitting on the
couch so that I was between his thighs. I had his cock between both my
hands as I was looking up to him, "that's it baby, you want to be treated
like a girl, well this is what girls do for their men, that's it, good
girl," Gregory whispered to me. I started by kissing the tip of his
cock, he had a beautiful head on him. I kissed it then made my way down
his shaft. Then I ran my tongue from the bottom on his shaft to the tip
of his cock, as he let out a moan. Now I was face to face with his head
and I simply opened my lips and slowly engulfed his cock. I began to slow
use my tongue on his veiny member as I bobbed up and down on his shaft. I
wasn't sure if I liked how his cock tasted in my mouth or the smell of his
manhood, but it wasn't that bad and as I continued to suck his cock. I
quickened my pace and I put more pressure on his cock with my lips, I was
very careful not to use my teeth. I had a good rhythm going for about
five minutes or so, when Gregory's breathing started to quicken. He let
on a moan and said he was about to cum. I was kinda surprised by this and
took my head up off of his cock. He then grabbed the back of my head and
pulled me back onto his cock, as he force my head to bop up and down. I
knew he was about to cum, but I wasn't sure I wanted to have him cum in my
mouth, let alone swallow his cum. I felt his cock tense up and he was
more forceful with his hand on the top of my head, there was no way I
could stop now. Then I could feel his cum hit the top of my mouth, it
wasn't much and it tasted salty, but they moments later a huge squirt of
come exploded in my mouth. He was holding my head down pretty well, and I
couldn't really move as his cum filled my mouth. "Oh ya, that's it baby
take all of my cum, that's my girl, swallow every last drop like a good
girl," he told me. I swallowed it all and once he was finished he let me
go. I stood up and he told me that if I was going to be a real girl that
I had to finish by cleaning his dick off. I told him I had to go, I was
pretty pissed off at this point. He told me that the night was still
young and that we can still have a lot of fun together. I told him I
didn't feel very well and that I thought it was best if I left. He
laughed and told me that he wanted me to stay but if I wanted to go, then
go. I grabbed my purse and hurried to the washroom. I rinsed my mouth
out with water and brushed my teeth. I still had to make it home so I
fixed my makeup to make myself more presentable.
Once I exited the washroom Gregory was waiting for me, he told me that he
would pay for a cab for me to get back to my car. I guess my emotions got
the best of me and I started to cry, I tried to hold back but I couldn't.
I just wanted to get home, I didn't want to get into a cab, what would the
cab driver think. I didn't really want to spend more time with Gregory
either but it was the less of two evils. He told me to relax, that I
didn't need to cry, he said that he would drive me back to my car. I told
him thank you and he joked that I really am a girl. On the car ride back
to my car, we didn't speak much. Right before I got out, Gregory
apologized to me, he told me he was sorry if he was too rough with me,
that he didn't mean to hurt me, or my feelings. I told him it was alright,
that I was just tired. I got out of the car, when Gregory put his window
down and told me, "you really do make a very convincing girl, you are very
pretty, and don't take this the wrong way, but you are one pretty good
cocksucker as well." I told him bye and I got into my car as he drove
off. I hurried on my way and made it home without any incidents. I got
undressed and took off all my makeup and jumped in the shower. Once I got
out of the shower and started to dry off I took a good look in the mirror.
I started to smile, because even though the night didn't go as planned and
I ended up getting pretty pissed off, I was able to get dressed up as a
girl and go on a date with a man. I did enjoy the attention I received
and I really liked being treated like a girl on a date, I enjoyed the
kissing and truth be told I did enjoy sucking his cock, for the most part.
I got changed into my pajamas and jumped into bed.
I wasn't sure if I would dress up again or if I would ever go on a date
with a man. I was pretty sure I wouldn't see Gregory again but the rest
was up in the air.
Goodnight!
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